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Literature DB >> 24862907

Novel product chemistry from mechanistic analysis of ent-copalyl diphosphate synthases from plant hormone biosynthesis.

Kevin Potter¹, Jared Criswell, Jiachen Zi, Alisha Stubbs, Reuben J Peters.

Abstract

An active-site water molecule coordinated by conserved histidine and asparagine residues seems to serve as the catalytic base in all ent-copalyl diphosphate synthases (CPSs). When these residues are substituted by alanine, the mutant CPSs produce stereochemically novel ent-8-hydroxy-CPP. Given the requisite presence of CPSs in all land plants for gibberellin phytohormone biosynthesis, such plasticity presumably underlies the observed extensive diversification of the resulting labdane-related diterpenoids.

Entities: CellLine Chemical Disease Gene Mutation Species

Keywords: biosynthesis; cyclization; enzyme catalysis; natural products; reaction mechanism

Mesh：

Substances：

Year: 2014 PMID： 24862907 PMCID： PMC4113509 DOI： 10.1002/anie.201402911

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

34 in total

1. Probing the role of the DXDD motif in Class II diterpene cyclases.

Authors: Sladjana Prisic; Jianjun Xu; Robert M Coates; Reuben J Peters
Journal: Chembiochem Date: 2007-05-25 Impact factor: 3.164

2. Following evolution's lead to a single residue switch for diterpene synthase product outcome.

Authors: Meimei Xu; P Ross Wilderman; Reuben J Peters
Journal: Proc Natl Acad Sci U S A Date: 2007-04-24 Impact factor: 11.205

3. A modular approach for facile biosynthesis of labdane-related diterpenes.

Authors: Anthony Cyr; P Ross Wilderman; Mara Determan; Reuben J Peters
Journal: J Am Chem Soc Date: 2007-05-05 Impact factor: 15.419

4. Identification and functional analysis of bifunctional ent-kaurene synthase from the moss Physcomitrella patens.

Authors: Ken-Ichiro Hayashi; Hiroshi Kawaide; Miho Notomi; Yuka Sakigi; Akihiko Matsuo; Hiroshi Nozaki
Journal: FEBS Lett Date: 2006-10-17 Impact factor: 4.124

5. Abietadiene synthase from grand fir (Abies grandis): characterization and mechanism of action of the "pseudomature" recombinant enzyme.

Authors: R J Peters; J E Flory; R Jetter; M M Ravn; H J Lee; R M Coates; R B Croteau
Journal: Biochemistry Date: 2000-12-19 Impact factor: 3.162

6. Synergistic substrate inhibition of ent-copalyl diphosphate synthase: a potential feed-forward inhibition mechanism limiting gibberellin metabolism.

Authors: Sladjana Prisic; Reuben J Peters
Journal: Plant Physiol Date: 2007-03-23 Impact factor: 8.340

7. Biological functions of ent- and syn-copalyl diphosphate synthases in rice: key enzymes for the branch point of gibberellin and phytoalexin biosynthesis.

Authors: Kazuko Otomo; Hiromichi Kenmoku; Hideaki Oikawa; Wilfried A König; Hiroaki Toshima; Wataru Mitsuhashi; Hisakazu Yamane; Takeshi Sassa; Tomonobu Toyomasu
Journal: Plant J Date: 2004-09 Impact factor: 6.417

8. ent-labdane glycosides from Baccharis pingraea.

Authors: C Zdero; F Bohlmann; H M Niemeyer
Journal: Phytochemistry Date: 1990 Impact factor: 4.072

9. Rice contains two disparate ent-copalyl diphosphate synthases with distinct metabolic functions.

Authors: Sladjana Prisic; Meimei Xu; P Ross Wilderman; Reuben J Peters
Journal: Plant Physiol Date: 2004-11-12 Impact factor: 8.340

10. Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture.

Authors: Anne Caniard; Philipp Zerbe; Sylvain Legrand; Allison Cohade; Nadine Valot; Jean-Louis Magnard; Jörg Bohlmann; Laurent Legendre
Journal: BMC Plant Biol Date: 2012-07-26 Impact factor: 4.215

26 in total

1. Combinatorial biosynthesis and the basis for substrate promiscuity in class I diterpene synthases.

Authors: Meirong Jia; Sambit K Mishra; Samuel Tufts; Robert L Jernigan; Reuben J Peters
Journal: Metab Eng Date: 2019-06-17 Impact factor: 9.783

2. A conserved amino acid residue critical for product and substrate specificity in plant triterpene synthases.

Authors: Melissa Salmon; Ramesha B Thimmappa; Robert E Minto; Rachel E Melton; Richard K Hughes; Paul E O'Maille; Andrew M Hemmings; Anne Osbourn
Journal: Proc Natl Acad Sci U S A Date: 2016-07-13 Impact factor: 11.205

Review 3. Structural and Chemical Biology of Terpenoid Cyclases.

Authors: David W Christianson
Journal: Chem Rev Date: 2017-08-25 Impact factor: 60.622

4. Conserved bases for the initial cyclase in gibberellin biosynthesis: from bacteria to plants.

Authors: Cody Lemke; Kevin C Potter; Samuel Schulte; Reuben J Peters
Journal: Biochem J Date: 2019-09-24 Impact factor: 3.857

5. Functional Divergence of Diterpene Syntheses in the Medicinal Plant Salvia miltiorrhiza.

Authors: Guanghong Cui; Lixin Duan; Baolong Jin; Jun Qian; Zheyong Xue; Guoan Shen; John Hugh Snyder; Jingyuan Song; Shilin Chen; Luqi Huang; Reuben J Peters; Xiaoquan Qi
Journal: Plant Physiol Date: 2015-06-15 Impact factor: 8.340

6. Catalytic Bases and Stereocontrol in Lamiaceae Class II Diterpene Cyclases.

Authors: Samuel Schulte; Kevin C Potter; Cody Lemke; Reuben J Peters
Journal: Biochemistry Date: 2018-05-31 Impact factor: 3.162

7. The genome of the medicinal plant Andrographis paniculata provides insight into the biosynthesis of the bioactive diterpenoid neoandrographolide.

Authors: Wei Sun; Liang Leng; Qinggang Yin; MeiMei Xu; Mingkun Huang; Zhichao Xu; Yujun Zhang; Hui Yao; Caixia Wang; Chao Xiong; Sha Chen; Chunhong Jiang; Ning Xie; Xilong Zheng; Ying Wang; Chi Song; Reuben J Peters; Shilin Chen
Journal: Plant J Date: 2019-01-02 Impact factor: 6.417